Ethanol → HCID 59377674, compound

HRID 1691790Notes

Reaction equation

HRID 1691790 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:19][CH2:20]O>>[CH2:19]([O:12][C:11](=[O:13])[CH2:10][C:3]1[CH:4]=[C:5]([OH:9])[C:6]([F:8])=[CH:7][C:2]=1[Br:1])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 59377673HCID 59377673, compound

Product 1

HCID 59377674HCID 59377674, compound

Procedure

To a solution of (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid (5.06 g) in EtOH (100 ml) was added sulfuric acid (0.2 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was heated at 70° C. with stirring for an additional 24 h. The mixture was evaporated to dryness under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc/9:1) gave (2-bromo-4-fluoro-5-hydroxy-phenyl)-acetic acid ethyl ester (4.66 g) as a solid.

Workup

  1. temperatureThe mixture was heated at 70° C.
  2. stirringwith stirring for an additional 24 h
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customPurification of the residue by flash chromatography (hexanes:EtOAc/9:1)

Sources & evidence

ORD record
ord-c73e3f524fe24ebcb4ed54d7acd43f2e
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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